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With sodium hydrogencarbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;
With diphenyl phosphoryl azide; triethylamine In tetrahydrofuran at 20℃; for 5h;
1.1 Step 1: 5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonyl azide
5-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (2.0 g, 10.2 mmol, 1.0 eq.) was dissolved in THF (20 mL), then TEA (1.7 mL, 12.3 mmol, 1.2 eq.) and DPPA (2.7 mL, 12.2 mmol, 1.2 eq.) were added. The resulting solution was stirred for 5 hour at ambient temperature and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/petroleum ether (1:5) to give 5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonyl azide (1.2 g) as a brown yellow solid.
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